Jackson Olson

Personality • Baseball Player

Birth Date: October 6, 1997

Age: 29 years old

Birth Place: New Milford, Connecticut

Partners: Maggie Sajak

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News aboutJackson Olson

Maggie Sajak asking boyfriend Jackson Olson if he wants to dance with her

‘Wheel of Fortune’ Fans Want Maggie Sajak On This Show After She Shows off Her Skills

Pat Sajak and Jackson Olson

November 5, 9:06 am

Pat Sajak Is Unimpressed by Jackson Olson’s Dance Moves on Family Trip

MAggie Sajak and Jackson Olson on thr set of "Wheel of Fortune" (left), (right) the couple at "Dancing with the Stars"

October 29, 2:22 pm

‘DWTS’ Jackson Olson Visits Girlfriend Maggie Sajak at ‘Wheel of Fortune’ After Elimination

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Jackson Olson and Guillermo Rodriguez

October 7, 9:38 am

‘Dancing With the Stars’: Guillermo Rodriguez Breaks Silence on Jackson Olson Controversy

Jackson Olson and Guillermo Rodriguez

October 6, 6:33 pm

‘DWTS’: Jackson Olson Apologizes to Guillermo Rodriguez After Controversial Comment

Jackson Olson, Emma Slater, Guillermo Rodriguez, Witney Carson

October 5, 10:33 am

‘Dancing With the Stars’: Jackson Olson & Guillermo Rodriguez Controversy, Explained

JACKSON OLSON

September 22, 11:39 am

‘Dancing With the Stars’: Are Jackson Olson’s Teeth Fake? He Explains

Harry Shum Jr., Tatyana Ali, Guillermo Rodriguez, 'Dancing With the Stars' Season 35 promo pics, ABC, premieres September 15, 2026.

September 10, 3:31 pm

Who Will Win ‘Dancing With the Stars’ Season 35? Looking at the Odds

Jackson Olson with girlfriend, Maggie Sajak

September 9, 2:53 pm

Maggie Sajak Debunks Rumor About How She Met Boyfriend Jackson Olson

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Maura Higgins and Mark Ballas, Brandon Armstrong and Ciara Miller, Daniella Karagach and Ezra Frech of Dancing With the Stars

September 2, 6:20 pm

Inside ‘Dancing With the Stars’ Season 35: Cast Reveals Ballroom Hopes & Rehearsal Updates

CARRIE ANN INABA, DEREK HOUGH, BRUNO TONIOLI

September 2, 8:22 am

‘Dancing With the Stars’ Season 35: Cast, Premiere Date & More to Know

Ciara MIller and Maura Higgins

September 2, 8:21 am

‘Dancing With the Stars’ Season 35 Cast: All 16 Celebrities Competing

Maggie Sajak sitting in a golf cart on a wine vineyard

July 7, 12:46 pm

‘Wheel of Fortune’ Fans Spot Maggie Sajak’s ‘Disgustingly Cute’ Tribute to Boyfriend

Maggie Sajak (right) with her boyfriend Jackson Olson (left) in Disney World

June 23, 11:10 am

Maggie Sajak’s Boyfriend Says He’s Found ‘The One’ in Emotional Post

Maggie Sajak and Jackson Olson

April 21, 4:45 pm

Who Is Maggie Sajak’s New Boyfriend? Meet Savannah Bananas’ Jackson Olson